Alkoxide-functionalized imidazolium betaines for CO2 activation and catalytic transformation

文献信息

发布日期 2013-12-20
DOI 10.1039/C3GC42346H
影响因子 10.182
作者

Yan-Bo Wang, Dong-Sheng Sun, Hui Zhou, Wen-Zhen Zhang, Xiao-Bing Lu


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摘要

Alkoxide-functionalized imidazolium betaines (AFIBs), including an alkoxide anion and an imidazolium cation, were synthesized by treating potassium tert-butoxide with 1-(2-hydroxyethyl)-2,3-disubstituted imidazolium bromide. The novel betaines were able to quickly capture CO2, affording carboxylate zwitterions (AFIB-CO2 adducts). In the presence of adventitious water, the transformation of the AFIB-CO2 adducts into the corresponding bicarbonate salts was observed by 1H and 13C NMR spectroscopy. The structures of the AFIB bicarbonate salts were solved using single crystal X-ray crystallography. Furthermore, the dithiocarboxylate zwitterions (AFIB-CS2 adducts), which are more stable to moisture in comparison with their CO2 adducts, were prepared by reacting CS2 with the corresponding betaines. X-Ray single crystal analysis revealed the bent geometry of the binding CS2 in the dithiocarboxylate zwitterions with a S–C–S angle of 126.6–126.9°, which indirectly confirms the structures of the AFIB-CO2 adducts in hand. These AFIB-CO2 adducts were found to function as organocatalysts for the coupling reaction of propargylic alcohols with CO2 for selectively producing valuable cyclic carbonates under mild and solvent-free reaction conditions.

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Green Chemistry

Green Chemistry
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Green Chemistry provides a unique forum for the publication of innovative research on the development of alternative green and sustainable technologies. The scope of Green Chemistry is based on, but not limited to, the definition proposed by Anastas and Warner (Green Chemistry: Theory and Practice, P T Anastas and J C Warner, Oxford University Press, Oxford, 1998). Green chemistry is the utilisation of a set of principles that reduces or eliminates the use or generation of hazardous substances in the design, manufacture and application of chemical products. Green Chemistry is at the frontiers of this continuously-evolving interdisciplinary science and publishes research that attempts to reduce the environmental impact of the chemical enterprise by developing a technology base that is inherently non-toxic to living things and the environment. Submissions on all aspects of research relating to the endeavour are welcome. The journal publishes original and significant cutting-edge research that is likely to be of wide general appeal. To be published, work must present a significant advance in green chemistry. Papers must contain a comparison with existing methods and demonstrate advantages over those methods before publication can be considered. For more information please see this Editorial. Coverage includes the following, but is not limited to: Design (e.g. biomimicry, design for degradation/recycling/reduced toxicity…) Reagents & Feedstocks (e.g. renewables, CO2, solvents, auxiliary agents, waste utilization…) Synthesis (e.g. organic, inorganic, synthetic biology…) Catalysis (e.g. homogeneous, heterogeneous, enzyme, whole cell…) Process (e.g. process design, intensification, separations, recycling, efficiency…) Energy (e.g. renewable energy, fuels, photovoltaics, fuel cells, energy storage, energy carriers…) Applications (e.g. electronics, dyes, consumer products, coatings, pharmaceuticals, preservatives, building materials, chemicals for industry/agriculture/mining…) Impact (e.g. safety, metrics, LCA, sustainability, (eco)toxicology…) Green chemistry is, by definition, a continuously-evolving frontier. Therefore, the inclusion of a particular material or technology does not, of itself, guarantee that a paper is suitable for the journal. To be suitable, the novel advance should have the potential for reduced environmental impact relative to the state of the art. Green Chemistry does not normally deal with research associated with 'end-of-pipe' or remediation issues.

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